READS

I'm writing this from a place that could almost be mistaken for the Italian countryside, were I not surrounded by lizards and toucans and bullfrogs the size of a fucking dinosaur.

Rather, I am high up in the hills of Central America overlooking the Costa Rican valley from my squishy, pancake lounger—it sort of reminds me of a bloated fat cat—while four other guests—two delightful gay couples—breast stroke around in the swimming pool below me and ponder how much it would cost to hire a private driver for the year. $20,000? $30,000? I wonder what they have done with their lives that has put them in such a privileged position to even ask a question like that.

Of course, self-important beast that I am, my thoughts quickly turn to my own life. Because aren't we always trying to triangulate who we are based on who everybody else is? I think about whether or not I could hire a private driver; whether I would even want one. It immediately strikes me as undesirable, and then straight-up scary to realize that something so pompous might fall squarely within my means. Who am I? Who is this middle-aged woman I'm becoming? (Note to self: never refer to self as “middle-aged” again.) Every day I am drifting farther and farther away from my original identity; every day I'm less and less the girl I grew up knowing. The narrative keeps changing. I keep evolving. And I am always someone I hardly recognize.

This is both reassuring and terrifying.

Reassuring, because I'll never have to experience the shame of need again, like I did when I was young. Terrifying, because metamorphosis, by definition, requires that you constantly become someone you weren't before.

I am never the same person, anymore, as I was five minutes ago. In that respect, I am always a stranger to myself—which can be a little disconcerting, but also the adventure of a lifetime. Having the opportunity to get to know yourself over and over again through a new lens gives you many chances to make things right with yourself. Growth feels like your mind is constantly a visitor in a foreign country—and maybe that's what I like about it. It can be a lonely place where you won't always speak the language, but that's part of the thrill: it is better to feel like an imposter in China, than a native in your living room. Home may be comforting, but comfort will always keep you small.

I suppose this is why I have come to love imposter syndrome—the nauseating feeling that we all get when we're exploring new lands. Unlike physical lands, however, these lands are mental. Starting the business. Stopping the business. Charging more money. Charging less. Taking the leap. Saying fuck yes—or no. Doing the thing. And being okay with not knowing what's going to happen afterward, or who it'll make you in the process.

I have come to think of every new experience as a new country to explore, and of course it's not going to feel natural. Of course you're going to feel like an imposter. It'd be bat shit crazy if you rolled up in Egypt all, “Yup, feel right at home!” Difference is going to make you feel different—and that applies to anything you try in your life and your work and your business and your everything. And what a wonderful opportunity, we all have, to feel that divergence. It is the opposite of stagnation. This is how, and when, we feel alive.

Imposter syndrome, then, is a sign of life. It's like the heart monitor you hear in the ER. It's a signal that you're not just rotting away in your living room along with the rest. You are a living, breathing, moving, learning, exploring, growing, wild, free-range human being—and yeah, that sound in your head is annoying, but it's also really important. Without it, you've flatlined.

As I sit here in Central America today, I feel whole, I feel challenged, and I also feel triumphant. I have just come from a month-long solo trip to South America; to Chile, where I learned how to harvest grapes on a vineyard outside of Patagonia, took drawing lessons from a Chilean artist in Valparaiso, did a photoshoot in the city with two renowned photographers, consulted on a famous soccer player's new business venture, worked with the U.S. Embassy to help nominate leaders for a new exchange program, helped a friend solidify her business plan as a freelance consultant, visited local businesses and craftsmen and artisans to see what kinds of interesting things they're creating, went to the ballet (and snuck in a Negroni in a mason jar), hiked through a new forest, had coffee in a stranger's home outside of aforementioned forest, did a private wine tasting in the offices of Calyptra vineyards (highly recommended if you've never had), explored all-new neighborhoods on foot, and celebrated THE BOOK DEAL around a bonfire with old and new friends alike—a Peruvian chef, a photographer from France, a student from Germany, a brilliant plastic surgeon, a diplomat, a robotics engineer, and several other entrepreneurs and politicians and creatives. And guess what? ALL of it made me feel, even if only momentarily, like an imposter. Who am I to harvest these grapes I know nothing about? (And what if I fuck it up?) Who am I to pick up a piece of charcoal and attempt to draw this teapot? (And what if I fuck it up?) Who am I to say what a world-famous soccer player should or should not do with his new digital business model? (And what if I fuck it up?) (Okay, fine, THAT I won't fuck up, because #EXPERIENCE.)

But could you imagine if I didn't do any of it because I was worried I'd look like a giant, ignorant douche rod?

Could you imagine if all I did was stay in my Airbnb and walk to get a coffee and keep my head down and try not to get robbed?

By doing the hard, we do our best.

There is so much richness in this life that we're all missing out on, every single day, because we're afraid we're going to fuck it up and look stupid and make giant a-holes out of ourselves. But the most embarrassing thing of all would be in letting your life pass you by without having any good stories to remind you who you are. It's not about the money or the recognition or the list of accomplishments you can put on your belt: it's about how your life has made you feel.

How do you want your life to feel?

My advice: chase imposter syndrome like the sun. Do everything that makes you second-guess yourself twice. Find the strange and the unusual and the uncomfortable and the new, and let her show you your own potential. Be brave enough to walk blind. Don't ask too many questions. Don't ask any, in fact. Stop censoring your own experience on this earth. Your safe harbor is only an illusion, anyway: at some point, we will all have our lives turned violently upside down, and your only defense is diversity. Diversity of experience, of relationships, of passions, of knowledge. When your soul knows many things, it is no longer afraid of loss. You can become a new person in the next five minutes. You can be someone you hardly recognize, anymore, and you can be okay with all of it.

Imposter syndrome isn't what we should be scared of: it's not feeling any at all.

The worst thing we can do is be afraid of looking silly, for it comes at the cost of our life.

2,083

READS

READS

So that happened this week. There’s a lot that could be said, and a lot I’ll refrain from saying, but I did want to send a courtesy note to say, first of all, that my new online business mentorship program is still moving forward—and starts tomorrow—and second, that holy moly, it’s about so much more […]

READS

By the end of the night, it was as if I had just had the best sex of my life, without so much as having shared a kiss. I knew nothing about him, except that I needed more. And more I got. Candlelit dinners, walks through parks, sensual kisses on street corners, and giggly phone […]

READS

A few years ago, there was this tacky term that made everybody cringe but also made everybody drool with wonder: lifestyle design. (Okay, fine, it was like ten years ago and I’m officially ancient.) The term always annoyed me, because it was widely represented by a bunch of twenty-something hopefuls traveling the world with their […]

READS

Q: Who’s Your Daddy? A: Novelty In the last year, two of the countries I’ve lived in are Chile & Costa Rica. In both places, I did a number of things, kissed met a number of people, and learned a number of lessons. Many people advocate the value of travel–that’s nothing new–but what they’re really […]

READS

You know why we’re all unhappy and restless and jaded and depressed? LIFE IS BORING US TO TEARS. Boredom is the devil, but most people don’t realize they’re bored. They’re busy working. They’re busy running. They’re busy doing ALL THE ERRANDS and keeping up with those fucksticks, The Jones’. It doesn’t feel like they’re bored, […]

READS

“I wish I could travel the world like you.” It was a comment left on a recent Facebook post, and admittedly, a comment I get often—but not one I like to receive. It depresses me, more than anything, how powerless most Westerners feel over their own lives. Anything is possible, in modern Western society, and […]

READS

So this past week, I took a motherfucking vacation. And do you know what? I’m going to take vacations all the time! It’s been decided! Vacations are just way too great to not take! Why aren’t people vacationing all the time? I hereby declare every last week of the month vacation week. Not only do […]

READS

I was pissed. It was 1998. I was 14. I had just put the finishing touches on my 90’s style bangs, sculpting and spraying them into the perfect 360 degree fan – you remember the kind where the top half curls backward, and the bottom half forward, right? (If you say no, that means you’re […]

READS

I sat in a plaza yesterday, behind La Moneda–Chile’s version of The White House. Diagonal paths come from all directions and meet up in the center, before darting off in opposite directions. People walk gruffly, generally ignoring one another–cell phones, busy faces, stern looks, fast paces. And just like in plazas everyday across the world… […]

READS

Yesterday was my birthday. I flew from Ecuador to Chile on Friday so I could spend my birthday with my best girl friends in the whole wide world. Sure enough, they surprised me in the airport with glittery welcome back posters, prompting me to scream like a hyena. I had no idea they were coming. […]

READS

There’s no such thing as luck, and if you’re banking your life on getting lucky, you might as well plan for the worst. In terms of lifestyle design, the word “design” implies “deliberate intention.” So if you want control over yours, it’s time to get up, get out there, and BE DELIBERATE AND INTENTIONAL.

READS

There are some people who don’t get the whole concept of an assembly line. You know who I’m talking about – those hanyacks at the Starbucks who come up beside you at the milk station, their panties in a bunch, tapping their foot, doing the hokey pokey at 8 o’clock in the morning because they […]

Exclusive VIP Access

Join The Middle Finger Project mafia—over 75,000+ disobedient humans strong—and as a welcome gift (which I promise won’t be a thug named Vinny), I’ll send you a top secret discount code for our best-selling courses, kits and workshops. Because #SOLIDARITY.

It’s free, and you’ll also get new posts every week, plus at least one GIF of Betty White for the win.